Alkyl 2-acetamido-2-deoxyglucopyranoside uronic acids and their preparation

ABSTRACT

Alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids, and their pharmaceutically or cosmetically acceptable salts, and their use as surface-active and/or interfacially active active compounds, in particular as detergent surfactants or emulsifiers.

The present invention relates to novel active compounds, theirpreparation and their use in the field of cosmetic and of pharmaceuticaldermatology. In particular, the present invention relates to activecompounds and cosmetic and dermatological preparations comprising suchactive compound combinations. In particular, the present inventionrelates to active compounds which have surfactant properties. Theinvention further relates to cosmetic and dermatological preparationswhich contain such substances. In a preferred embodiment, the presentinvention relates to cosmetic cleansing agents.

Agents of this type are known per se. In this context, they areessentially surface-active substances or substance mixtures which areoffered to the consumer in various preparations.

Preparations of this type are, for example, bubble baths and showerbaths, solid and liquid soaps or so-called "syndets" (syntheticdetergents), shampoos, hand-washing pastes, intimate cleansing agents,special cleansing agents for infants and the like.

Surface-active substances--the best-known of which are the alkali metalsalts of the higher fatty acids, i.e. the classical "soaps"--areamphiphilic substances which can emulsify, organic non-polar substancesin water.

These substances wash not only dirt from the skin and hair; depending onthe choice of the surfactant or of the surfactant mixture, they irritatethe skin and mucous membranes to a greater or lesser degree. The mostuseful surfactant for cosmetic cleansing agents is sodium lauryl ethersulphate. Although it has good washing power and--depending ondosage--is very highly skin--and mucous membrane-tolerable, sensitivepersons should avoid frequent contact with it.

There are admittedly a large number of very mild surfactants available,but the surfactants of the prior art are either mild, but cleansepoorly, or else they cleanse well, but irritate the skin or mucousmembranes.

Cosmetic emulsions also contain interfacially active substances,so-called emulsifiers. These reduce the surfaces of contact between thephases and form oil/water interfacial films on the phase boundary. As aresult, the irreversible confluence of the dispersed phase iscounteracted.

Efficient emulsifiers are therefore distinguished by a very goodemulsifying, solubilizing and dispersing ability. To a great extent, itis desirable that such substances do not cause skin irritation. Thechoice of such substances known to the prior art is restricted. it wastherefore an object of the present invention to enrich the prior art inthis respect.

Advantageous cleansing formulations, even within the meaning of thepresent invention, are shower preparations.

Preparations of this type are known per se. In this context, they areessentially surface-active substances or substance mixtures which areoffered to the consumer in various preparations. Preparations of such atype are in general distinguished by a high water content to a greateror lesser degree, but can also be present, for example, as aconcentrate.

In general, preparations which are intended for the shower bath do notdiffer or hardly differ from bath preparations apart from the fact thatin the case of shower preparations products of higher viscosity arepreferred, which do not run from the hand after removal from thecontainer. In the case of bath preparations, this is less of practicalimportance.

Even in the case of a simple water bath without addition of surfactants,a swelling of the horny layer of the skin first occurs, the degree ofthis swelling, for example, depending on the duration of the bath andits temperature. At the same time, water-soluble substances, e.g.water-soluble dirt constituents, but also substances endogenous to theskin, which are responsible for the water-binding power of the hornylayer, are washed off or washed out. As a result of surface-activesubstances endogenous to the skin, skin oils are additionally alsodissolved to a certain extent and washed out. After initial swelling,this causes a subsequent marked drying out of the skin, which can beincreased by detergent additives.

In healthy skin, these processes are in general unimportant, as theprotective mechanisms of the skin can compensate for such slightdisturbances of the upper skin layers without problem. However, even inthe case of non-pathological variations from the normal status, e.g. asa result of environmentally related wear and tear and irritations,damage due to light, presbyderma, etc., the protective mechanism of theskin surface is disturbed. Under certain circumstances, it is then nolonger able by itself to fulfil its objects and must be regenerated byexternal measures.

The prior art is acquainted with oil bath preparations of various types,it being possible to vary the properties of the fat or oil phase byaddition of surface-active substances. In this case, depending on thenature and amount of the constituents chosen, preparations can beformulated which either produce spreading oil films, oil-in-watersystems or even total solubilizates on the bath-water surface. Foamingformulations, but also only slightly foaming or non-foamingformulations, are possible. In general, the functionality ofpreparations of this type is restricted in oil bath or oil cream bathpreparations to the refatting or superfatting of the uppermost layers ofskin.

Nevertheless, caring oils can in isolated cases at best cover up theharmful effect of a not very skin-friendly surfactant, which is why anoil bath or an oil cream bath cannot be better than the surfactant(s)employed therein.

It was thus the object of the present invention to remedy the defects ofthe prior art in this respect.

In a further preferred embodiment, the present invention relates tocosmetic and dermatological preparations for the prophylaxis andtreatment of cosmetic or dermatological cell changes, in particular skinchanges such as, for example, skin ageing, in particular the cell ageingcaused by oxidative processes, in particular skin ageing.

Finally, it was an object of the present invention to conceivepreparation processes for such active compounds.

It was surprising and not to be foreseen by the person skilled in theart that alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids of thegeneral formula ##STR1## where R is representative of the groupconsisting of branched and unbranched alkyl of 1-48 C atoms, inparticular of 14-22, preferably 16-18, C atoms, and their salts, and aprocess for the preparation of alkyl2-acetamido-2-deoxy-D-glucopyranoside uronic acids of the generalformula ##STR2## where R is representative of the group consisting ofbranched and unbranched alkyl of 1-48 C atoms, in particular of 14-22,preferably 16-18, C atoms, and their salts, characterized in that

(1) chitin is ground

(2) the ground chitin is treated with acid and a first aliphatic alcoholof low chain length, preferably of a chain length of less than C₈,whereupon

(3) if desired the reaction product thus obtained is purified bydialysis, preferably electrodialysis,

(4) a second alcohol not identical to the first aliphatic alcohol,preferably of a chain length of C₈ and longer, is reacted with thereaction product under acid catalysis, whereby the first aliphaticalcohol becomes free again and

(4a) if desired is removed by distillation,

(5) the reaction product is subjected to oxidation,

and the alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids ortheir salts obtained in this process and the novel intermediates in thisprocess eliminate all outlined disadvantages of the prior art.

Consequently, also according to the invention is the use of alkyl2-acetamido-2-deoxy-D-glucopyranaside uronic acids of the generalformula ##STR3## where R is representative of the group consisting ofbranched and unbranched alkyl of 1-48 C atoms, in particular of 14-22,preferably 16-18, C atoms, as surface-active and/or interfacially activeactive compounds, in particular as detergent surfactants or emulsifiers,and where the uronic acids can preferably be present in the form oftheir salts, in particular as alkali metal salts, of these preferablythe sodium salt, or as ammonium, alkylammonium, dialkylammonium,trialkylammonium or tetraalkylammonium salts.

The substances obtained according to the invention are distinguished byoutstanding skin-friendliness, very good surface-active andinterfacially active activity and processability in cosmetic anddermatological preparations.

Mixtures of α- and β-glycosides can also be advantageous according tothe invention. In any case, a plethora of processes which are able toseparate the anomers are known to the person skilled in the art, forexample chromatographic processes.

The alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids and theiradvantageous salts according to the invention are derived formally aswell as practically from chitin, which is characterized by thestructural formula ##STR4## Chitin is an essential constituent of theexoskeleton ['οχιτων=Grk.: armoured jacket] of the arthropods (e.g.insects, crabs, spiders) and is also found in supportive tissues ofother organisms (e.g. molluscs, algae, fungi)

The use of chitin derivatives, namely of chitosan, a hydrolysis productof chitin, in cosmetic preparations is known per se. Chitosan, forexample, is better suited than the chitin on which it is based, as athickener or stabilizer and improves the adhesion and water-resistanceof polymeric films. Representing a multiplicity of places where this isfound in the prior art: H. P. Fiedler, "Lexikon der Hilfstoffe furPharmazie, Kosmetik und angrenzende Gebiete" [Encyclopedia ofauxiliaries for pharmacy, cosmetics and neighbouring fields], 4thEdition 1989, Editio Cantor, Aulendorf, p. 349, headword "Chitosan".

The use of other sugar derivatives as surface-active substances incosmetics, dermatics and other preparations has also been thoroughlydisclosed, for example in the Patent Application Documents WO 93/07249,German Offenlegungsschrift 41 29 124, German Offenlegungsschrift 41 02502, German Offenlegungsschrift 40 26 471 and German Offenlegungsschrift40 26 809.

Nevertheless, it was not possible for the prior art to make any hint atthe present invention.

According to the invention, a process is advantageously used which ismodelled on the following reaction scheme: ##STR5##

Particularly advantageous reaction conditions provide that

(2) the ground chitin is treated in the presence of heat, advantageouslyat temperatures of 40-70° C., in particular about 55° C., with acid anda first aliphatic alcohol.

Particularly advantageous reaction conditions provide that

(4) a second alcohol not identical to the first aliphatic alcohol,preferably of a chain length of C₈ and longer, is reacted with thereaction product under acid catalysis, as a result of which the firstaliphatic alcohol becomes free again and

(4a) is removed in vacuo by distillation.

A suitable temperature range for this reaction step and for thedistillative removal of the first aliphatic alcohol is between 80 and100° C., preferably about 90° C.

The acid catalysis can be carried out on acidic ion-exchange resins,e.g. Amberlite IR 120, by means of camphorsulphonic acid or hydrochloricacid.

At the end of this reaction step, a neutralisation can advantageously becarried out, e.g. using sodium hydroxide solution or on basicion-exchange resins.

It is furthermore advantageous

(5) to subject the reaction product to oxidation with Pt/O₂ (Adam'scatalyst).

According to the invention, an anomer mixture is obtainable which can beseparated into the anomers by methods familiar to the person skilled inthe art. According to the invention, mainly the α-anomer is obtained,usually in a nine-fold excess compared with the β-anomer.

It can also be advantageous to start from commercially available alkyl2-acetamido-2-deoxyglucopyranosides and only to carry out the reactionstep (5) according to the reaction scheme ##STR6##

It has further emerged that the alkyl2-acetamido-2-deoxyglucopyranosides which are known per se are alsooutstandingly suitable as surface-active or interfacially activesubstances. Therefore, also according to the invention is the use ofalkyl 2-acetamido-2-deoxyglucopyranosides of the general structuralformula ##STR7## where R is representative of the group consisting ofbranched and unbranched alkyl of 1-48 C atoms, in particular of 14-22,preferably 16-18, C atoms, as surface-active and/or interfacially activeactive compounds, in particular as detergent surfactants or emulsifiers.

The cosmetic or dermatological formulations according to the inventioncan be made up in the customary manner and used for the treatment, thecare and the cleansing of the skin and/or the hair and as a make-upproduct in decorative cosmetics. They preferably contain 0.001% byweight to 10% by weight, but in particular 0.01% by weight to 6% byweight, based on the total weight of the composition, of the alkyl2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to theinvention.

For use, the cosmetic and dermatological preparations according to theinvention are applied to the skin and/or the hair in adequate amounts inthe manner customary for cosmetics.

Cosmetic and dermatological preparations according to the invention canbe present in various forms. Thus it is possible to prepare, forexample, a solution, an anhydrous preparation, an emulsion ormicroemulsion of the type water-in-oil (W/O) or of the type oil-in-water(O/W), a multiple emulsion, for example of the typewater-in-oil-in-water (W/O/W), a gel, a solid stick, an ointment oralternatively an aerosol.

It is also possible and advantageous within the meaning of the presentinvention to add the alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronicacids according to the invention to aqueous systems or surfactantpreparations for cleansing the skin and the hair.

The cosmetic and dermatological preparations according to the inventioncan contain cosmetic auxiliaries, such as are customarily used in suchpreparations, e.g. preservatives, bactericides, perfumes, substances forpreventing foaming, colourants, pigments which have a colouring action,thickening agents, surface-active substances, emulsifiers, emollient,moisturizing and/or moisture-retaining substances, fats, oils, waxes orother customary constituents of a cosmetic or dermatological formulationsuch as alcohols, polyols, polymers, foam stabilizers, electrolytes,organic solvents or silicone derivatives.

In particular, the alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronicacids can also be combined with antioxidants.

According to the invention, convenient antioxidants which can be usedare all antioxidants suitable or customary for cosmetic and/ordermatological applications.

Advantageously, the antioxidants are selected from the group consistingof amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and theirderivatives, imidazoles (e.g. urocaninic acid) and their derivatives,peptides such as D,L-carnosine, D-carnosine, L-carnosine and theirderivatives (e.g. anserine), carotenoids, carotenes (e.g. α-carotene,β-carotene, lycopene) and their derivatives, chlorogenic acid and itsderivatives, lipoic acid and its derivatives (e.g. dihydrolipoic acid),aurothioglucose, propylthiouracil and other thiols (e.g. thioredoxin,glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl,methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl,γ-linoleyl, cholesteryl and glyceryl esters) and also their salts,dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionicacid and its derivatives (esters, ethers, peptides, lipids, nucleotides,nucleosides and salts) as well as sulphoximine compounds (e.g.buthionine sulphoximine, homocystein sulphoximine, buthionine sulphone,penta-, hexa and heptathionine sulphoximine) in very low tolerable doses(e.g. pmol to μmol/kg), furthermore (metal) chelators (e.g. α-hydroxyfatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids(e.g. citric acid, lactic acid, maleic acid), humic acid, bile acid,bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives,unsaturated fatty acids and their derivatives (e.g. γ-linolenic acid,linoleic acid, oleic acid), folic acid and its derivatives, ubiquinoneand ubiquinol and their derivatives, vitamin C and derivatives (e.g.ascorbyl palmitate, Mg-ascorbyl phosphate, ascorbyl acetate),tocopherols and derivatives (e.g. vitamin E acetate), vitamin A andderivatives (vitamin A palmitate) as well as coniferyl benzoate ofbenzoin, rutic acid and its derivatives, α-glycosylrutin, ferulic acid,furfurylidenglucitol, carnosine, butylhydroxytoluene,butylhydroxyanisole, nordihydroguairetic acid, trihydroxybutyrophenone,uric acid and its derivatives, mannose and its derivatives, zinc and itsderivatives (e.g. ZnO, ZnSO₄), selenium and its derivatives (e.g.selenomethionine), stilbenes and their derivatives (e.g. stilbene oxide,trans-stilbene oxide) and the suitable derivatives according to theinvention (salts, esters, ethers, sugars, nucleotides, nucleosides,peptides and lipids) of these mentioned active compounds.

The amount of the abovementioned antioxidants (one or more compounds) inthe preparations is preferably 0.001 to 300% by weight, particularlypreferably 0.05-20% by weight, in particular 1-10% by weight, based onthe total weight of the preparation.

If vitamin E and/or its derivatives are the antioxidant(s), it isadvantageous to select their respective concentrations from the rangefrom 0.001-10% by weight, based on the total weight of the formulation.

If vitamin A, or vitamin A derivatives, or carotenes or theirderivatives are the antioxidant(s) it is advantageous to select theirrespective concentrations from the range from 0.001-100% by weight,based on the total weight of the formulation.

Emulsions according to the invention are advantageous and contain, forexample, the fats, oils, waxes and other fatty materials mentioned, aswell as water and an emulsifier, such as is customarily used for such atype of formulation.

The lipid phase can in this case advantageously be selected from thefollowing substance group:

natural, synthetic and/or partially synthetic oils, such astriglycerides of capric or of caprylic acid, but preferably castor oil;

fats, waxes and other natural synthetic and/or partially synthetic fattymaterials, preferably esters of fatty acids with alcohols of low Cnumber, e.g. with isopropanol, propylene glycol or glycerol, or estersof fatty alcohols with alkanoic acids of low C number or with fattyacids;

silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes,diphenylpolysiloxanes as well as mixed forms thereof;

saturated compounds such as hydrocarbons of natural or synthetic origin(petroleum jelly, squalane).

The aqueous phase of the preparations according to the invention ifdesired advantageously contains alcohols, diols or polyols of low Cnumber, as well as their ethers, preferably ethanol, isopropanol,propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethylor monobutyl ether, propylene glycol monomethyl, monoethyl or monobutylether, diethylene glycol monomethyl or monoethyl ether and analogousproducts and also, in particular, one or more thickening agents, whichcan advantageously be selected from the group consisting of silica,aluminium silicates, polysaccharides and their derivatives, e.g.hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose, particularlyadvantageously from the group consisting of the polyacrylates,preferably a polyacrylate from the group consisting of the so-calledcarbopols, for example carbopols of the types 980, 981, 1382, 2984,5984, in each case individually or in combination.

In particular, mixtures of the abovementioned solvents are used. In thecase of alcoholic solvents water can be a further constituent.

Gels according to the invention customarily contain alcohols of low Cnumber, e.g. ethanol, isopropanol, 1,2-propanediol, glycerol and wateror an above-mentioned oil in the presence of a thickening agent which inthe case of oily-alcoholic gels is preferably silica or an aluminiumsilicate, and in the case of aqueous-alcoholic or alcoholic gelspreferably a polyacrylate.

Suitable propellants for preparations according to the invention whichcan be sprayed from aerosol containers are the customary known easilyvolatile, liquefied propellants, for example hydrocarbons (propane,butane, isobutane), which can be employed on their own or as a mixturewith one another. Compressed air can also advantageously be used.

Advantageously, preparations according to the invention can additionallycontain substances which absorb UV radiation in the UVB range, the totalamount of the filter substances being, for example, 0.1% by weight to30% by weight, preferably 0.5 to 10% by weight, in particular 1.0 to6.0% by weight, based on the total weight of the preparations, in orderto make available cosmetic preparations which protect the hair or theskin from the entire range of ultraviolet radiation. They can also beused as sunscreens for the hair or the skin.

If the emulsions according to the invention contain UVB filtersubstances, these can be oil-soluble or water-soluble. Advantageousoil-soluble UVB filters according to the invention are, for example:

3-benzylidencamphor derivatives, preferably3-(4-methylbenzylidene)camphor, 3-benzylidenecamphor;

4-aminobenzoic acid derivatives, preferably 2-ethylhexyl4-dimethylaminobenzoate, amyl 4-dimethylaminobenzoate;

esters of cinnamic acid, preferably 2-ethylhexyl 4-methoxycinnamate,isopentyl 4-methoxycinnamate;

esters of salicylic acid, preferably 2-ethylhexyl salicylate,4-isopropylbenzyl salicylate, homomenthyl salicylate;

derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone,2-hydroxy-4-methoxy-4'-methylbenzophenone,2,2'-dihydroxy-4-methoxybenzophenone;

esters of benzylidenemalonic acid, preferably di(2-ethylhexyl)4-methyoxybenzylidenemalonate,2,4,6-trianilino-(p-carbo-2'-ethyl-1'-hexyloxy)-1,3,5-triazine.

Advantageous water-soluble UVB filters are, for example:

salts of 2-phenylbenzimidazole-5-sulphonic acid such as its sodium,potassium or its triethanolammonium salt, as well as the sulphonic aciditself;

sulphonic acid derivatives of benzophenone, preferably2-hydroxy-4-methoxybenzophenone-5-sulphonic acid and its salts;

sulphonic acid derivatives of 3-benzylidenecamphor, such as, forexample, 4-(2-oxo-3-bornylidenemethyl)-benzenesulphonic acid,2-methyl-5-(2-oxo-3-bornylidenemethyl)sulphonic acid and their salts.

The list of the UVB filters mentioned, which can be used in combinationwith the alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acidsaccording to the invention, should of course be non-limiting.

The invention also relates to the use of a combination of the alkyl2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to theinvention with at least one UVB filter as antioxidant or the use of acombination of the tocopherylglycosides according to the invention withat least one UVB filter as antioxidant in a cosmetic or dermatologicalpreparation.

It can also be advantageous to combine alkyl2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to theinvention with UVA filters which to date are customarily contained incosmetic preparations. These substances are preferably derivatives ofdibenzoylmethane, in particular1-(4'-tert-butylphenyl)-3-(4'-methoxyphenyl)propane-1,3-dione and1-phenyl-3-(4'-isopropylphenyl)propane-1,3-dione. These combinations andpreparations which contain these combinations are also a subject of theinvention. The amounts used for the UVB combination can be employed.

The invention also relates to the use of a combination of the alkyl2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to theinvention with at least one UVA filter as antioxidant or the use of acombination of the tocopherylgycosides according to the invention withat least one UVA filter as antioxidant in a cosmetic or dermatologicalpreparation.

The invention also relates to the use of a combination of the alkyl2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to theinvention with at least one UVA filter and at least one UVB filter asantioxidant or the use of a combination of the tocopherylglycosidesaccording to the invention with at least one UVA filter and at least oneUVB filter as antioxidant in a cosmetic or dermatological preparation.

Cosmetic and dermatological preparations having an efficacious contentof alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids according tothe invention can also contain inorganic pigments which are customarilyused in cosmetics for the protection of the skin from UV rays. In thiscase, these are oxides of titanium, zinc, iron, zirconium, silicon,manganese, aluminium, cerium and mixtures thereof, as well asmodifications in which the oxides are the active agents. Particularlypreferably, they are pigments based on titanium dioxide.

These combinations of UVA filter and pigment or preparations whichcontain this combination are also a subject of the invention. Theamounts mentioned for the above combinations can be used.

Cosmetic and dermatological preparations for the protection of the hairfrom UV rays according to the invention are, for example, shampoos,preparations which are applied when rinsing the hair before or aftershampooing, before or after permanent wave treatment, or before or afterdyeing or bleaching hair, preparations for hot-air drying or setting ofthe hair, preparations for dyeing or bleaching, a hairdressing andtreatment lotion, a hair lacquer or permanent wave compositions.

The cosmetic and dermatological preparations contain active compoundsand auxiliaries, such as are customarily used for this type ofpreparations for hair care and hair treatment. Auxiliaries used arepreservatives, surface-active substances, substances for preventingfoaming, thickening agents, emulsifiers, fats, oils, waxes, organicsolvents, bactericides, perfumes, dyes or pigments whose object is tocolour the hair or the cosmetic or dermatological preparation itself,electrolytes and substances preventing the hair from becoming greasy.

Electrolytes within the meaning of the present invention arewater-soluble alkali metal, ammonium, alkaline earth metal (includingmagnesium) and zinc salts of inorganic anions and any desired mixturesof those salts, where it must be guaranteed that these salts aredistinguished by pharmaceutical or cosmetic acceptability.

The anions according to the invention are preferably selected from thegroup consisting of the chlorides, the sulphates and hydrogen sulphates,the phosphates, hydrogen phosphates and the linear and cyclicoligophosphates as well as the carbonates and hydrogen carbonates.

Cosmetic preparations which are a skin-cleansing agent or shampoopreferably contain at least one further anionic, non-ionic or amphotericand surface-active substance or surface-active betaines, oralternatively mixtures of such substances, furthermore alkyl2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to theinvention in aqueous medium and auxiliaries, such as are customarilyused for this purpose. The surface-active substance or the mixtures ofthese substances can be present in a concentration of between 1% byweight and 50% by weight in the shampoo.

If the cosmetic or dermatological preparations are present in the formof a lotion which is rinsed out and is applied, for example, before orafter bleaching, before or after shampooing, between two shampooingsteps, or before or after permanent wave treatment, they are in thiscase, for example, aqueous or aqueous-alcoholic solutions whichoptionally contain surface-active substances whose concentration can bebetween 0.1 and 10% by weight, preferably between 0.2 and 5% by weight.

These cosmetic or dermatological preparations can also be aerosolscontaining the auxiliaries customarily used for this purpose.

A cosmetic preparation in the form of a lotion which is not rinsed out,in particular a lotion for setting the hair, a lotion which is usedduring hot-air drying of the hair, or a hairdressing and treatmentlotion, is in general an aqueous, alcoholic or aqueous-alcoholicsolution and contains at least one cationic, anionic, non-ionic oramphoteric polymer or alternatively mixtures thereof, as well as activecompound combinations according to the invention in an efficaciousconcentration. The amount of the polymers used is, for example, between0.1 and 10% by weight, preferably between 0.1 and 3% by weight.

Cosmetic preparations for the treatment and care of the skin and of thehair, which contain alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronicacids according to the invention can be present as emulsions which areof the non-ionic or cationic type. Besides water, non-ionic emulsionscontain oils or fatty alcohols which, for example, can also bepolyethoxylated or polypropoxylated, or alternatively mixtures of bothorganic components. These emulsions optionally contain cationicsurface-active substances.

According to the invention, cosmetic preparations for the treatment andcare of the hair can also be present as gels which, besides anefficacious content of alkyl 2-acetamido-2-deoxy-D-glucopyranosideuronic acids according to the invention, preferably contain water,further organic thickening agents, e.g. gum arabic, xanthan gum, sodiumalginate, cellulose derivatives, preferably methylcellulose,hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose,hydroxypropylmethylcellulose or inorganic thickening agents, e.g.aluminium silicates such as, for example, bentonites, or a mixture ofpolyethylene glycol and polyethylene glycol stearate or distearate. Thethickening agent is contained in the gel, for example, in an amount ofbetween 0.1 and 30% by weight, preferably of between 0.5 and 15% byweight.

Preferably, the amount of the alkyl2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to theinvention in a composition intended for the hair is 0.05% by weight to10% by weight, in particular 0.5% by weight to 5% by weight, based onthe total weight of the composition.

Aqueous cosmetic cleansing agents according to the invention orcleansing agent concentrates which are low in water or water-freeintended for aqueous cleansing can contain anionic, non-ionic and/oramphoteric surfactants, for example conventional soaps, e.g. fatty acidsalts of sodium, alkyl sulphates, alkyl ether sulphates, alkane- andalkylbenzenesulphonates, sulphoacetates, sulphobetaines, sarcosinates,amidosulphobetaines, sulphosuccinates, sulphosuccinic acid monoesters,alkyl ether carboxylates, protein-fatty acid condensates, alkylbetainesand amidobetaines, fatty acids alkanolamides and/or polyglycol etherderivatives.

Cosmetic preparations which are cosmetic cleansing preparations for theskin can be present in liquid or solid form. Besides the alkyl2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to theinvention or their salts, they can preferably contain at least oneanionic, non-ionic or amphoteric surface-active substance or mixturesthereof, and if desired one or more electrolytes and auxiliaries, suchas are customarily used for this purpose. The surface-active substancecan be present in a concentration of between 1 and 94% by weight in thecleansing preparations, based on the total weight of the preparations.

Besides an efficacious content of alkyl2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to theinvention or their salts, cosmetic preparations which are a shampoopreferably contain at least one anionic, non-ionic or amphotericsurface-active substance or mixtures thereof, and if desired anelectrolyte and auxiliary according to the invention, such as arecustomarily used for this purpose. The surface-active substance can bepresent in a concentration of between 1% by weight and 94% by weight inthe shampoo.

Apart from the abovementioned surfactants, the compositions according tothe invention contain water and, if desired, the additives customary incosmetics, for example perfume, thickener, colourants, antimicrobialsubstances, refatting agents, complexing and sequestering agents, pearllustre agents, plant extracts, vitamins, active compounds and the like.

Preferably, the amount of alkyl 2-acetamido-2-deoxy-D-glucopyranosideuronic acids used according to the invention in these preparations is0.001% by weight to 10% by weight, in particular 0.1% by weight to 3% byweight, based on the total weight of the preparations.

The invention also relates to the process for the preparation of thecosmetic compositions according to the invention, which is characterizedin that alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids areincorporated into cosmetic and dermatological formulations in a mannerknown per se.

The following examples are intended to explain the present inventionwithout restricting it.

PREPARATION EXAMPLE 1

Stearyl 2-acetamido-2-deoxy-D-glucopyranoside Uranic Acid Na Salt

Ground chitin is treated at 55° C. with hydrochloric acid and butylalcohol and the reaction product thus obtained is purified byelectrodialysis. The reaction product is reacted with stearyl alcoholwith acid catalysis with camphorsulphonic acid at 90° C. and the butylalcohol is stripped off under a water-jet vacuum at 90° C. The productis neutralized with NaOH and the product is oxidized to the finalproduct at 60° C. using Adam's catalyst.

PREPARATION EXAMPLE 2

Cetyl 2-acetamido-2-deoxy-D-glucopyranoside Uranic Acid Na Salt

Ground chitin is treated at 55° C. with hydrochloric acid and butylalcohol and the reaction product thus obtained is purified byelectrodialysis. The reaction product is reacted with cetyl alcohol withacid catalysis with camphorsulphonic acid at 90° C. and the butylalcohol is stripped off under a water-jet vacuum at 90° C. The productis neutralized with NaOH and the product is oxidized to the finalproduct at 60° C. using Adam's catalyst.

PREPARATION EXAMPLE 3

Decyl 2-acetamido-2-deoxy-D-glucopyranoside Uronic Acid Na Salt

Ground chitin is treated at 55° C. with hydrochloric acid and butylalcohol and the reaction product thus obtained is purified byelectrodialysis. The reaction product is reacted with decyl alcohol withacid catalysis with camphorsulphonic acid at 90° C. and the butylalcohol is stripped off under a water-jet vacuum at 90° C. The productis neutralized with NaOH and the product is oxidized to the finalproduct at 60° C. using Adam's catalyst.

PREPARATION EXAMPLE 4

Dodecyl 2-acetamido-2-deoxy-D-glucopyranoside Uronic Acid Na Salt

Ground chitin is treated at 55° C. with hydrochloric acid and butylalcohol and the reaction product thus obtained is purified byelectrodialysis. The reaction product is reacted with dodecyl alcoholwith acid catalysis with camphorsulphonic acid at 90° C. and the butylalcohol is stripped off under a water-jet vacuum at 90° C. The productis neutralized with NaOH and the product is oxidized to the finalproduct at 60° C. using Adam's catalyst.

PREPARATION EXAMPLE 5

Tetradecyl 2-acetamido-2-deoxy-D-glucopyranoside Uronic Acid Na Salt

Ground chitin is treated at 55° C. with hydrochloric acid and butylalcohol and the reaction product thus obtained is purified byelectrodialysis. The reaction product is reacted with tetradecyl alcoholwith acid catalysis with camphorsulphonic acid at 90° C. and the butylalcohol is stripped off under a water-jet vacuum at 90° C. The productis neutralized with NaOH and the product is oxidized to the finalproduct at 60° C. using Adam's catalyst.

PREPARATION EXAMPLE 6

Palmityl 2-acetamido-2-deoxy-D-glucopyranoside Uronic Acid Na Salt

Ground chitin is treated at 55° C. with hydrochloric acid and butylalcohol and the reaction product thus obtained is purified byelectrodialysis. The reaction product is reacted with palmityl alcoholwith acid catalysis with camphorsulphonic acid at 90° C. and the butylalcohol is stripped off under a water-jet vacuum at 90° C. The productis neutralized with NaOH and the product is oxidized to the finalproduct at 60° C. using Adam's catalyst.

PREPARATION EXAMPLE 7

Eicosyl 2-acetamido-2-deoxy-D-glucopyranoside Uronic Acid Na Salt

Ground chitin is treated at 55° C. with hydrochloric acid and butylalcohol and the reaction product thus obtained is purified byelectrodialysis. The reaction product is reacted with eicosyl alcoholwith acid catalysis with camphorsulphonic acid at 90° C. and the butylalcohol is stripped off under a water-jet vacuum at 90° C. The productis neutralized with NaOH and the product is oxidized to the finalproduct at 60° C. using Adam's catalyst.

EXAMPLE 1

    ______________________________________                                                               % by                                                     (O/W emulsion): weight                                                      ______________________________________                                        Cetyl 2-acetamido-2-deoxy-D-glucopyran-                                                              0.75                                                     oside uronic acid Na salt                                                     Sorbitan stearate 2.00                                                        Petroleum jelly 1.0                                                           Paraffin oil, subliquidum 11.00                                               Octyldodecanol 4.00                                                           Hydrogenated coconut fatty acid glycerides 1.00                               Carbomer 2984 0.15                                                            Glycerol 3.00                                                                 Sorbitol 1.00                                                                 Panthenol 1.00                                                                Tocopheryl acetate 1.25                                                       Bisabolol 0.10                                                                Perfume, preservative, q.s.                                                   colourants, antioxidants                                                      Water to 100.00                                                             ______________________________________                                    

EXAMPLE 2

    ______________________________________                                                               % by                                                     (W/O emulsion): weight                                                      ______________________________________                                        Stearyl 2-acetamido-2-deoxy-D-glucopyran-                                                            0.15                                                     oside uronic acid Na salt                                                     PEG-7 hydrogenated castor oil 4.00                                            Wool wax alcohol 1.50                                                         Beeswax 3.00                                                                  Petroleum jelly 9.00                                                          Ozocerite 4.00                                                                Paraffin oil, subliquidum 10.00                                               Glycerol 3.00                                                                 Sorbitol 1.00                                                                 Panthenol 1.00                                                                Tocopheryl acetate 1.25                                                       Bisabolol 0.10                                                                Magnesium sulphate 7H.sub.2 O 0.70                                            Perfume, preservative, q.s.                                                   colourants, antioxidants                                                      Water to 100.00                                                             ______________________________________                                    

EXAMPLE 3

    ______________________________________                                                              % by                                                      (Hydrodispersion gel): weight                                               ______________________________________                                        Cetyl 2-acetamido-2-deoxy-D-glucopyran-                                                             0.25                                                      oside uronic acid Na salt                                                     PEG-8 (polyethylene glycol 400) 5.00                                          Ethanol 2.00                                                                  Carbomer 2984 0.70                                                            Triglyceride, liquid 1.50                                                     Glycerol 4.00                                                                 Sorbitol 1.00                                                                 Panthenol 0.50                                                                Tocopheryl acetate 0.50                                                       Perfume, preservative, q.s.                                                   colourants, antioxidants                                                      Water to 100.00                                                             ______________________________________                                    

EXAMPLE 4

    ______________________________________                                                              % by                                                      (O/W emulsion): weight                                                      ______________________________________                                        Cetyl 2-acetamido-2-deoxy-D-glucopyran-                                                             2.00                                                      oside uronic acid Na salt                                                     Glycerol monostearate 2.00                                                    Petroleum jelly 1.00                                                          Paraffin oil, subliquidum 11.00                                               Octyldodecanol 4.00                                                           Hydrogenated coconut fatty acid 1.00                                          glycerides                                                                    Carbomer 2984 0.15                                                            Glycerol 3.00                                                                 Sorbitol 1.00                                                                 Panthenol 1.00                                                                Tocopheryl acetate 1.25                                                       Bisabolol 0.10                                                                Perfume, preservative, q.s.                                                   colourants, antioxidants                                                      Water to 100.00                                                             ______________________________________                                    

EXAMPLE 5

    ______________________________________                                                               % by                                                     (W/O emulsion): weight                                                      ______________________________________                                        Stearyl 2-acetamido-2-deoxy-D-glucopyran-                                                            0.25                                                     oside uronic acid Na salt                                                     PEG 7 hydrogenated castor oil 4.00                                            Wool wax alcohol 1.50                                                         Beeswax 3.00                                                                  Petroleum jelly 9.00                                                          Ozocerite 4.00                                                                Paraffin oil, subliquidum 10.00                                               Glycerol 3.00                                                                 Sorbitol 1.00                                                                 Panthenol 1.00                                                                Tocopheryl acetate 1.25                                                       Bisabolol 0.10                                                                Magnesium sulphate 7 H.sub.2 O 0.70                                           Perfume, preservative, q.s.                                                   colourants, antioxidants                                                      Water to 100.00                                                             ______________________________________                                    

EXAMPLE 6

    ______________________________________                                                              % by                                                      (Hydrodispersion gel): weight                                               ______________________________________                                        Cetyl 2-acetamido-2-deoxy-D-glucopyran-                                                             0.15                                                      oside uronic acid Na salt                                                     PEG 8 (polyethylene glycol 400) 5.00                                          Ethanol 2.00                                                                  Carbomer 2984 0.70                                                            Triglyceride, liquid 1.50                                                     Glycerol 4.00                                                                 Sorbitol 1.00                                                                 Panthenol 0.50                                                                Tocopheryl acetate 0.50                                                       Perfume, preservative, q.s.                                                   colourants, antioxidants                                                      Water to 100.00                                                             ______________________________________                                    

EXAMPLE 7

    ______________________________________                                                              % by                                                      Shampoo weight                                                              ______________________________________                                        Cetyl 2-acetamido-2-deoxy-D-glucopyran-                                                              5.00                                                     oside uronic acid Na salt                                                     Sodium lauryl ether sulphate (27.5%) 25.00                                    Sodium chloride q.s.                                                          Pearl lustre agent q.s.                                                       Perfume, preservative, q.s.                                                   colourants, antioxidants                                                      Water to 100.00                                                             ______________________________________                                    

EXAMPLE 8

    ______________________________________                                                               % by                                                     Shampoo weight                                                              ______________________________________                                        Stearyl 2-acetamido-2-deoxy-D-glucopyran-                                                             4.00                                                    oside uronic acid Na salt                                                     Alkylpolyglucose (50%) 25.00                                                  Sodium chloride q.s.                                                          Pearl lustre agent q.s.                                                       Perfume, preservative, q.s.                                                   colourants, antioxidants                                                      Water to 100.00                                                             ______________________________________                                    

EXAMPLE 9

    ______________________________________                                                               % by                                                     Shampoo weight                                                              ______________________________________                                        Stearyl 2-acetamido-2-deoxy-D-glucopyran-                                                            5.00                                                     oside uronic acid Na salt                                                     Sodium lauryl ether sulphate (27.5%) 14.00                                    Alkylpolyglucose (50%) 8.00                                                   Sodium chloride q.s.                                                          Pearl lustre agent q.s.                                                       Perfume, preservative, q.s.                                                   colourants, antioxidants                                                      Water to 100.00                                                             ______________________________________                                    

EXAMPLE 10

    ______________________________________                                                               % by                                                     Face cleansing/washing lotion weight                                        ______________________________________                                        Stearyl 2-acetamido-2-deoxy-D-glucopyran-                                                             5.00                                                    oside uronic acid Na salt                                                     Sodium cocoamidoacetate (30%) 10.00                                           Perfume, preservative, q.s.                                                   colourants, antioxidants                                                      Water to 100.00                                                             ______________________________________                                    

EXAMPLE 11

    ______________________________________                                                                % by                                                    Clear shower bath weight                                                    ______________________________________                                        Palmityl 2-acetamido-2-deoxy-D-glucopyran-                                                            5.00                                                    oside uronic acid Na salt                                                     Sodium lauryl ether sulphate (27.5%) 25.00                                    Alkylpolyglucose (50%) 4.00                                                   Pearl lustre agent q.s.                                                       Sodium chloride q.s.                                                          Perfume, preservative, q.s.                                                   colourants, antioxidants                                                      Water to 100.00                                                             ______________________________________                                    

We claim:
 1. An alkyl 2-acetamido-2deoxy-D-glucopyranoside uronic acidcompound of the formula ##STR8## where R represents a branched orunbranched alkyl having from 8 to 48 carbon atoms, or a pharmaceuticallyor cosmetically acceptable salt of said uronic acid compound.
 2. Analkyl 2 acetamido-2-deoxy-D-glucopyranoside uronic acid according toclaim 1, wherein R represents an alkyl group having from 10 to 48 carbonatoms.
 3. An alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acidaccording claim 1 wherein R represents an alkyl group having from 14 to22 carbon atoms.
 4. An alkyl 2-acetamido-2-deoxy-D-glucopyranosideuronic acid according to claim 1, which is in the form of a salt.
 5. Analkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acid according toclaim 4, wherein the salt is selected from the group consisting ofalkali metal, ammonium, alkylammonium, dialkylammonium, trialkylammoniumand tetraalkylammonium salts.
 6. A process for preparing an alkyl2-acetamido-2-deoxy-D-glucopyranoside uronic acid compound of theformula: ##STR9## wherein R represents branched or unbranched alkylhaving 8 to 48 carbon atoms;or a pharmaceutically or cosmeticallyacceptable salt of said uronic acid compound; said process comprising:a)grinding chitin; b) reacting the ground chitin with an acid and a firstaliphatic alcohol having up to 8 carbon atoms, to yield a first reactionproduct; c) optionally purifying said first reaction product by dialysisto yield a purified first reaction product; d) reacting said firstreaction product or said purified first reaction with a second aliphaticalcohol having 8 to 48 carbon atoms, wherein said second aliphaticalcohol is different from said first aliphatic alcohol, and saidreaction between said first reaction product or said purified firstreaction product and said second aliphatic alcohol is under acidcatalysis to yield a third reaction product and said first aliphaticalcohol; e) optionally removing said first aliphatic alcohol bydistillation to yield a purer third reaction product; and f) oxidizingsaid third reaction product or said purer third reaction product toyield said uronic acid compound.
 7. Process according to claim 6,wherein said chitin, in step b) is reacted at 40-70° C.
 8. Processaccording to claim 6, wherein said first reaction product in step c) ispurified by electrodialysis.
 9. Process according to claim 6, whereinsaid second aliphatic alcohol in step d) is reacted at 80-100° C.